Azo compound and polarizing film

Abstract

The present invention is concerned with a novel azo compound represented by formula (1), (2) or (3), a water-soluble dye comprising this azo compound, and a polarizing film containing this azo compound. The obtained polarizing film has high hydrothermoresistance and a high polarization degree and is excellent in optical characteristics: ##STR1## wherein each of the groups is defined.

Claims

1. An azo compound represented by formula (2): ##STR73## wherein each of R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, carboxyl group, sulfonic group or chlorine atom; R.sub.12 is a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 carbon atoms; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

2. The azo compound according to claim 1 wherein R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, phenylamino group or benzoylamino group.

3. An azo compound represented by formula (3): ##STR74## wherein each of R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylanino group; R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, carboxyl group, sulfonic group or chlorine atom; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

4. The azo compound according to claim 3 wherein R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, phenylamino group or benzoylamino group.

5. A water-soluble dye which comprises an azo compound represented by formula (2) or (3): ##STR75## wherein each of R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, alkyl group having 1 or 2 carbon atoms, carboxyl group, sulfonic group or chlorine atom; R.sub.12 is a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 carbon atoms; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

6. An integrated film comprising a protective film or layer on a surface of a polarizing film which comprises a polymer film containing an azo compound represented by formula (1), (2) or (3) which is oriented therein: ##STR76## wherein each of R.sub.1, R.sub.3 and R.sub.12 is independently a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.2, R.sub.4, R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.5 is a hydroxyl group or amino group at the o-position or p-position to the azo group; each of R.sub.6 and R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.7 and R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, alkyl group having 1 or 2 carbon atoms, carboxyl group, sulfonic group or chlorine atom; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

7. An integrated film comprising a transparent electroconductive film of indium-tin oxide on a surface of a polarizing film which comprises a polymer film containing an azo compound represented by formula (1), (2) or (3) which is oriented therein: ##STR77## wherein each of R.sub.1, R.sub.3 and R.sub.12 is independently a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.2, R.sub.4, R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.5 is a hydroxyl group or amino group at the o-position or p-position to the azo group; each of R.sub.6 and R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.7 and R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, alkyl group having 1 or 2 carbon atoms, carboxyl group, sulfonic group or chlorine atom; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

8. A method for preparing a polarizing film which comprises the step of stretching a polymer film at a stretch ratio of from 2 times to 9 times, said polymer film being dyed with a water-soluble dye which comprises an azo compound represented by formula (1), (2) or (3): ##STR78## wherein each of R.sub.1, R.sub.3 and R.sub.12 is independently a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 atoms; each of R.sub.2, R.sub.4, R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.5 is a hydroxyl group or amino group at the o-position or p-position to the azo group; each of R.sub.6 and R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.7 and R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, alkyl group having 1 or 2 carbon atoms, carboxyl group, sulfonic group or chlorine atom; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.

9. A method for preparing a polarizing film which comprises the steps of stretching a polymer film at a stretch ratio of from 2 times to 9 times and dyeing the stretched film with a water-soluble dye which comprises an azo compound represented by formula (1), (2) or (3): ##STR79## wherein each of R.sub.1, R.sub.3 and R.sub.12 is independently a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 atoms; each of R.sub.2, R.sub.4, R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.5 is a hydroxyl group or amino group at the o-position or p-position to the azo group; each of R.sub.6 and R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.7 and R.sub.11 is a hydrogen atom, hydroxyl group, amino group, methylamino group,.beta.-hydroxyethylamino group, acetylamino group, or phenylamino or benzoylamino group in which the phenyl nucleus may be substituted by a nitro group, amino group, hydroxyl group, alkyl group having 1 or 2 carbon atoms, carboxyl group, sulfonic group or chlorine atom; p is 0 or 1; q is 0, 1 or 2; and M is copper, nickel, zinc or iron.